5,230

Chester, MD Homes

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  • /106

    $799,000

    Sold Sep 15, 2026

    136 Nauset Ln, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,986 Sq Ft
    • Built 2021

    Last Sold Summary

    • $268/SF
    • 0 Days On Market

    Current Estimated Value $835,122

    Last Listing Agent Heather Taylor RE/MAX One

    136 Nauset Ln, Chester, MD 21619
    • /55

      Not Listed For Sale

      211 Switchgrass Way Unit 1511, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 2,000 Sq Ft
      • Built 2024
      211 Switchgrass Way Unit 1511, Chester, MD 21619

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /50

    $5,400,000

    $500K PRICE DROP Pending
    • 7 Beds
    • 9 Baths
    • 10,667 Sq Ft

    330 Serenity Ln, Chester, MD 21619

    Designed to rival a private resort, this waterfront estate was built for celebrating with family and friends. Sweeping Chesapeake views set the stage for every gathering. The waterfront pool features a cascading rock waterfall, a tucked in bench, and a generous sun shelf, all overlooked by a pool house with a covered summer kitchen, bar, seating area, and full bath with AC. A curated firepit

    Brad Kappel TTR Sotheby's International Realty

    330 Serenity Ln, Chester, MD 21619
  • /48

    $559,900

    Sold May 27, 2026

    630 Warbler Way Unit 2223, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2025

    Last Sold Summary

    • $295/SF
    • 35 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2223, Chester, MD 21619
    • /48

      Not Listed For Sale

      212 Switchgrass Way Unit 1632, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      • Built 2024
      212 Switchgrass Way Unit 1632, Chester, MD 21619

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /23

    $524,999

    $25K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    230 Switchgrass Way Unit 12, Chester, MD 21619

    NEW INCENTIVE — THE OWNERS WILL COVER YOUR $8,000 COMMUNITY BUY-IN WITHACCEPTABLE OFFER!Move-in ready condo with zero wait! This meticulously maintained, first-floor Magothy shows likenew, offering over 2,000 square feet of single-level living in the highly sought-after FourSeasons at Kent Island 55+ active-adult community. Enjoy the rare convenience of directoutdoor patio

    David Moore Real Broker, LLC

    230 Switchgrass Way Unit 12, Chester, MD 21619
  • /34

    $280,000

    Sold Apr 17, 2026

    106 Merganser Ct, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft
    • Built 1999

    Last Sold Summary

    • 2% Below List Price
    • $262/SF
    • 1 Day On Market

    Current Estimated Value $280,626

    Last Listing Agent Crystal Smith RE/MAX Executive

    106 Merganser Ct, Chester, MD 21619
    • /51

      Not Listed For Sale

      218 Peregrine Dr, Chester, MD 21619

      • 3 Beds
      • 3 Baths
      • 2,772 Sq Ft
      • Built 2024
      218 Peregrine Dr, Chester, MD 21619

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /46

    $349,900

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    54F Queen Caroline Ct, Chester, MD 21619

    Completely remodeled in 2026 with a new kitchen to include new appliances, quartz counters, and backsplash, 3 new bathrooms, all new flooring throughout, new washer and dryer and freshly painted. Nestled in the serene enclave of Queens Landing, this exquisite remodeled in 2026 Colonial townhouse offers a harmonious blend of luxury and comfort. Spanning 1,440 square feet, the open floor plan

    Lawrence Doyle Long & Foster Real Estate, Inc.

    54F Queen Caroline Ct, Chester, MD 21619
  • /21

    $869,990

    Sold Jul 22, 2026

    102 Boatswain Way Unit 21, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 3% Below List Price
    • $334/SF
    • 71 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    102 Boatswain Way Unit 21, Chester, MD 21619
    • /42

      Not Listed For Sale

      228 Warbler Way, Chester, MD 21619

      • 4 Beds
      • 3 Baths
      • 2,791 Sq Ft
      • Built 2024
      228 Warbler Way, Chester, MD 21619

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /14

    $749,990

    New Construction $50K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    723 Warbler Way, Chester, MD 21619

    Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point.A dedicated home office provides a private space for work or study, while

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    723 Warbler Way, Chester, MD 21619
  • /63

    $365,000

    Sold Oct 20, 2025

    1033 Dundee Ct Unit 5, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,360 Sq Ft
    • Built 2003

    Last Sold Summary

    • $268/SF
    • 14 Days On Market

    Current Estimated Value $354,397

    Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

    1033 Dundee Ct Unit 5, Chester, MD 21619
    • /51

      Not Listed For Sale

      111 Peregrine Dr, Chester, MD 21619

      • 3 Beds
      • 3 Baths
      • 2,772 Sq Ft
      • Built 2024
      111 Peregrine Dr, Chester, MD 21619

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /56

    $609,990

    New Construction Pending
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 2912, Chester, MD 21619

    Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces.The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets,

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2912, Chester, MD 21619
  • /28

    $285,000

    Sold May 05, 2026

    1905 Bayside Dr, Chester, MD 21619

    • 2 Beds
    • 1.5 Baths
    • 1,220 Sq Ft
    • Built 1976

    Last Sold Summary

    • 21% Below List Price
    • $234/SF
    • 17 Days On Market

    Current Estimated Value $360,772

    Last Listing Agent Lisa Ciofani Cummings & Co. Realtors

    1905 Bayside Dr, Chester, MD 21619
    • /51

      Not Listed For Sale

      211 Warbler Way, Chester, MD 21619

      • 3 Beds
      • 3 Baths
      • 2,772 Sq Ft
      • Built 2024
      211 Warbler Way, Chester, MD 21619

      Last Sold Summary

      • 86 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /40

    $318,500

    $31K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,312 Sq Ft

    45G Queen Neva Ct, Chester, MD 21619

    Price Improvement! Seller is offering closing cost assistance for qualified buyers! This charming townhouse in Queens Landing offers a perfect blend of comfort and community amenities. Step inside to discover a traditional floor plan featuring a cozy living room off the eat-in kitchen, with a separate family room ideal for gatherings. The home boasts two spacious bedrooms and 2.5 baths, including

    John Freeman Coldwell Banker Realty

    45G Queen Neva Ct, Chester, MD 21619
  • /27

    $899,990

    Sold Mar 04, 2026

    141 Redstart Dr, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 14% Below List Price
    • $325/SF
    • 13 Days On Market

    Current Estimated Value $896,393

    K. Hovnanian Homes Four Seasons at Kent Island - Single Family

    141 Redstart Dr, Chester, MD 21619
    • /76

      Not Listed For Sale

      129 Wheelhouse Way Unit 2032, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      • Built 2024
      129 Wheelhouse Way Unit 2032, Chester, MD 21619

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Creig Northrop Northrop Realty

  • /56

    $485,000

    $3K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    1000 Herons Nest Way Unit 22, Chester, MD 21619

    BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE.This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. Easy walk to Kayak launch and creek. With nearly 2000 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area

    Ralph Kennedy RE/MAX Executive

    1000 Herons Nest Way Unit 22, Chester, MD 21619
  • /36

    $705,000

    Sold Sep 23, 2025

    242 Peregrine Dr, Stevensville, MD 21666

    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft
    • Built 2024

    Last Sold Summary

    • $224/SF
    • 111 Days On Market

    Last Listing Agent Pamela Owens Anchor Group Realty, LLC

    242 Peregrine Dr, Stevensville, MD 21666
    • /53

      Not Listed For Sale

      1 F S Queen Victoria Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,260 Sq Ft
      • Built 1983
      1 F S Queen Victoria Ct, Chester, MD 21619

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Peter Ayerle Cummings & Co. Realtors

  • /44

    $949,990

    New Construction $90K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    110 Boatswain Way Unit 3041, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in November 2026, this home combines modern style with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. The owner’s suite includes a sitting room and large walk-in closets, providing a

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3041, Chester, MD 21619
  • /23

    $350,000

    Sold Feb 06, 2026

    1839 Harbor Dr, Chester, MD 21619

    • 4 Beds
    • 2 Baths
    • 2,035 Sq Ft
    • Built 1975

    Last Sold Summary

    • $172/SF
    • 119 Days On Market

    Current Estimated Value $364,018

    Last Listing Agent Greg Koch Taylor Properties

    1839 Harbor Dr, Chester, MD 21619
    • /49

      Est $393,925

      Not Listed For Sale

      203 Dominion Ln, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,074 Sq Ft
      • Built 2017
      203 Dominion Ln, Chester, MD 21619

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Jim Davidson Coldwell Banker Waterman Realty

  • /49

    $515,000

    $20K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,000 Sq Ft

    205 Anchor Ln, Chester, MD 21619

    SPACE, FLEXIBILITY & VALUE ON KENT ISLAND! Welcome to 205 Anchor Lane, where generous square footage, versatile two-level living and incredible outdoor space come together to create a home that can truly adapt to your needs. With 5 bedrooms, updated bathrooms and living spaces on both levels, the floor plan offers excellent flexibility for multi-generational living, guests, a home office or the

    Kathleen Higginbotham Samson Properties

    205 Anchor Ln, Chester, MD 21619
  • /29

    $899,990

    Sold Jun 04, 2026

    307 Kingfisher Ln, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 8% Below List Price
    • $325/SF
    • 8 Days On Market

    Current Estimated Value $882,700

    K. Hovnanian Homes Four Seasons at Kent Island - Single Family

    307 Kingfisher Ln, Chester, MD 21619
    • /71

      Est $947,501

      Not Listed For Sale

      360 Macum Creek Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 3,225 Sq Ft
      • Built 2012
      360 Macum Creek Dr, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Tara Trout Samson Properties

  • /51

    $999,990

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    110 Boatswain Way Unit 3044, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home blends modern comfort with functional living spaces.The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    110 Boatswain Way Unit 3044, Chester, MD 21619
  • /48

    $514,990

    Sold May 18, 2026

    630 Warbler Way Unit 2222, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2025

    Last Sold Summary

    • $271/SF
    • 107 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2222, Chester, MD 21619
    • /3

      Not Listed For Sale

      lot 16 & 17 Cecil Dr, Chester, MD 21619

      lot 16 & 17 Cecil Dr, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • /65

    $989,000

    Under Contract
    • 5 Beds
    • 4 Baths
    • 2,752 Sq Ft

    2702 Sherman Dr, Chester, MD 21619

    Discover the extraordinary waterfront oasis of 2702 Sherman Dr. in Chester. This remarkable residence, featuring 5 bedrooms, 2 full bathrooms, and 2 half bathrooms, has undergone a stunning renovation, creating a haven of luxury and serenity on a peaceful street. Every detail of this home has been impeccably updated, from the oversized windows to the modernized bathrooms. However, the true

    Justin Kennedy Samson Properties

    2702 Sherman Dr, Chester, MD 21619
  • /48

    $350,000

    Sold Aug 14, 2026

    7013 Bridgepointe Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,635 Sq Ft
    • Built 1993

    Last Sold Summary

    • 7% Below List Price
    • $214/SF
    • 31 Days On Market

    Current Estimated Value $377,844

    Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

    7013 Bridgepointe Dr, Chester, MD 21619
    • /9

      Not Listed For Sale

      26K Queen Anne Way Unit 26K, Chester, MD 21619

      • 1 Bed
      • 1 Bath
      • 640 Sq Ft
      • Built 1983
      26K Queen Anne Way Unit 26K, Chester, MD 21619

      Last Sold Summary

      Last Listing Agent John Cary Rosendale Realty

  • /19

    $739,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    211 Switchgrass Way Unit 31, Chester, MD 21619

    Striking gourmet kitchen with designer cabinets & chef-worthy island.Elegant dining area featuring fancy dry bar.Refined great room featuring stunning fireplace.Serene owner's suite with maginificnet sitting room & walk-in closets.Owner's spa bath with dual sinks and lavish shower.Wonderful balcony for relaxing outdoors.

    K. Hovnanian Homes Builder
    211 Switchgrass Way Unit 31, Chester, MD 21619
  • /65

    $740,000

    Sold Jan 09, 2026

    123 Bentons Pleasure Rd, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,791 Sq Ft
    • Built 2002

    Last Sold Summary

    • $265/SF
    • 23 Days On Market

    Current Estimated Value $767,525

    Last Listing Agent Tricia Wilson Wilson Realty & Staging LLC

    123 Bentons Pleasure Rd, Chester, MD 21619
    • /28

      Not Listed For Sale

      33 F Queen Anne Way, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,680 Sq Ft
      • Built 1988
      33 F Queen Anne Way, Chester, MD 21619

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Alex Martinez The Agency DC

  • /56

    $619,990

    New Construction $10K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 2911, Chester, MD 21619

    Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces.The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets,

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2911, Chester, MD 21619
  • /48

    $612,500

    Sold May 28, 2026

    630 Warbler Way Unit 2232, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2025

    Last Sold Summary

    • $322/SF
    • 78 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2232, Chester, MD 21619

Showing Results 161 - 200, Page 5 of 18

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